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This is a discussion of a case that goes awry and finds a solution in the psychoanalyst’s use of free associative writing as a means of looking inward in the hope of finding a new and more authentic way to resonate with the experience of the patient. While many patients find the analyst’s insight and empathy sufficient for the therapeutic experience they seek, the patient discussed in this paper needed to feel that I had lived something of what had generated his difficulties in the world. I didn’t think I had until writing free associatively put me in touch with experiences that proved to be of vital importance to our work.